3,5-Bis(trifluoromethyl)benzyl bromide → HCID 86613813, compound

HRID 2378137Notes

Reaction equation

HRID 2378137 reaction equation
[CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[N:12][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:14][CH:15]=2)[C@H:10]([NH:21][C:22](=[O:24])[CH3:23])[CH2:9][C@@H:8]1[CH:25]1[CH2:27][CH2:26]1)=[O:6])([CH3:3])[CH3:2].[F:28][C:29]([F:43])([F:42])[C:30]1[CH:31]=[C:32]([CH:35]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:37]=1)[CH2:33]Br.C[Si](C)(C)[N-][Si](C)(C)C.[Li+]>>[CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[N:12][C:13]([C:17]([F:20])([F:18])[F:19])=[CH:14][CH:15]=2)[C@H:10]([N:21]([C:22](=[O:24])[CH3:23])[CH2:33][C:32]2[CH:35]=[C:36]([C:38]([F:40])([F:41])[F:39])[CH:37]=[C:30]([C:29]([F:28])([F:42])[F:43])[CH:31]=2)[CH2:9][C@@H:8]1[CH:25]1[CH2:26][CH2:27]1)=[O:6])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 1225733,5-Bis(trifluoromethyl)benzyl bromideHCID 2733832Lithium HexamethyldisilazideHCID 86613814HCID 86613814, compound

Product 1

HCID 86613813HCID 86613813, compoundYield 35%

Procedure

Prepare the title compound by essentially following the procedure described in Example 49, Step 2, by replacing (+/−)-N-(1-cyclopently-6-methoxy-2-methyl-1,2,3,4-tetrahydro-[1,5]napthyridin-4-yl)-acetamide, with (+/−)-cis-4-acetylamino-2-cyclopropyl-6-trifluoromethyl-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid isopropyl ester (0.075 g, 0.019 mmol), and using 3,5-bis trifluoromethyl benzyl bromide and lithium hexamethyldisilazide. Purify by silica gel column chromatography (gradient eluent, neat ethyl acetate) to afford the title compound (0.042 g, 35%). MS (ES+): 612 (M+H).

Workup

  1. customPurify by silica gel column chromatography (gradient eluent, neat ethyl acetate)

Sources & evidence

ORD record
ord-c57db58bbfcf4e13b572544343fc9ae9
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

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